Efficient organocatalytic asymmetric synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives

被引:83
|
作者
Gao, Yu [1 ]
Yang, Wen [1 ]
Du, Da-Ming [1 ]
机构
[1] Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE MICHAEL ADDITION; HYDROGEN-BONDING DONORS; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; AQUEOUS-MEDIA; BIFUNCTIONAL ORGANOCATALYSTS; CONJUGATE ADDITION; CHIRAL SQUARAMIDES; NITROALKENES; THIOUREA;
D O I
10.1016/j.tetasy.2012.02.019
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The organocatalytic enantioselective tandem Michael addition-cyclization of malononitrile to nitroalkenes for the direct synthesis of chiral 2-amino-4H-chromene-3-carbonitrile derivatives was investigated. Good yields and enantioselectivities (up to 91% ee) were achieved. This organocatalytic asymmetric tandem Michael addition-cyclization provides an efficient route toward the synthesis of optically active functionalized chromenes. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:339 / 344
页数:6
相关论文
共 50 条
  • [41] 2-Aminopyrazine catalyzed three-component and one-pot construction of 2-amino-4H-chromene-3-carbonitrile by mortar-pestle grinding and molecular docking studies
    Edapu, Harish Kumar
    Boodida, Sathyanarayana
    Pagadala, Ramakanth
    Damera, Thirupathi
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2024, 71 (02) : 240 - 247
  • [42] Enantioselective synthesis of 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile derivatives by Fe3O4@PS-arginine as an efficient chiral magnetic nanocatalyst
    Karkhah, Maryam Kargar
    Kefayati, Hassan
    Shariati, Shahab
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (10)
  • [43] ULTRASONIC ASSISTED SYNTHESIS AND OPTIMIZATION OF 2-AMINO-4H-CHROMENE'S DERIVATIVES
    Patel, Sarika
    Patel, Shweta
    Vaghani, Hasit
    Kumbhani, Jasmin
    Bhola, Ravibhai
    HETEROCYCLIC LETTERS, 2022, 12 (01): : 101 - 108
  • [44] Antimicrobial effects of new designed 2-amino-tetrahydro-4H-chromene-3-carbonitrile derivatives against some pathogenic microbial strains
    Moshafi M.H.
    Doostishoar F.
    Jahanian A.
    Abaszadeh M.
    Comparative Clinical Pathology, 2016, 25 (6) : 1197 - 1200
  • [45] Crystal structure of 2-amino-7-hydroxy-4-(4-hydroxyphenyl)-4H-chromene-3-carbonitrile
    Horton, Peter N.
    Akkurt, Mehmet
    Mohamed, Shaaban K.
    Younes, Sabry H. H.
    Albayati, Mustafa R.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O546 - +
  • [46] Functionalization of magnetic nanoparticles by creatine as a novel and efficient catalyst for the green synthesis of 2-amino-4H-chromene derivatives
    Reza Eivazzadeh-Keihan
    Shahrzad Bahrami
    Mostafa Ghafori Gorab
    Zahra Sadat
    Ali Maleki
    Scientific Reports, 12
  • [47] Functionalization of magnetic nanoparticles by creatine as a novel and efficient catalyst for the green synthesis of 2-amino-4H-chromene derivatives
    Eivazzadeh-Keihan, Reza
    Bahrami, Shahrzad
    Gorab, Mostafa Ghafori
    Sadat, Zahra
    Maleki, Ali
    SCIENTIFIC REPORTS, 2022, 12 (01)
  • [49] Synthesis and Crystal Structure of 2-Amino-5,6-dihydro-4-(3,4-dimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile
    ZHUANG QiYaa b WU Nana SHI DaQinga b TU ShuJianga b a Department of Chemistry Xuzhou Normal University Xuzhou China b Key Laboratory of Biotechnology on Medical Plants of Jiangsu Province Xuzhou China
    结构化学, 2006, (07) : 775 - 778
  • [50] Synthesis and crystal structure of 2-amino-5,6-dihydro-4-(3,4-dimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile
    Zhuang Qi-Ya
    Wu Nan
    Shi Da-Qing
    Tu Shu-Hang
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2006, 25 (07) : 775 - 778